JP4365584B2 - ビス−トリフルイミド化合物に触媒される方法 - Google Patents
ビス−トリフルイミド化合物に触媒される方法 Download PDFInfo
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- JP4365584B2 JP4365584B2 JP2002571437A JP2002571437A JP4365584B2 JP 4365584 B2 JP4365584 B2 JP 4365584B2 JP 2002571437 A JP2002571437 A JP 2002571437A JP 2002571437 A JP2002571437 A JP 2002571437A JP 4365584 B2 JP4365584 B2 JP 4365584B2
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- Prior art keywords
- reaction
- catalyst
- bis
- triflimide
- metal
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- AHXNYDBSLAVPLY-UHFFFAOYSA-M 1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methanesulfonimidate Chemical class [O-]S(=O)(=NS(=O)(=O)C(F)(F)F)C(F)(F)F AHXNYDBSLAVPLY-UHFFFAOYSA-M 0.000 title claims abstract description 53
- 238000000034 method Methods 0.000 title claims abstract description 36
- 229910052751 metal Inorganic materials 0.000 claims abstract description 64
- 239000002184 metal Substances 0.000 claims abstract description 64
- 150000002739 metals Chemical class 0.000 claims abstract description 12
- 239000003446 ligand Substances 0.000 claims abstract description 7
- 230000007935 neutral effect Effects 0.000 claims abstract description 6
- 230000008569 process Effects 0.000 claims abstract description 5
- 229910052768 actinide Inorganic materials 0.000 claims abstract description 4
- 150000001255 actinides Chemical class 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims description 155
- 239000003054 catalyst Substances 0.000 claims description 140
- 239000002608 ionic liquid Substances 0.000 claims description 81
- -1 bistriflimide anion Chemical class 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 19
- 150000001491 aromatic compounds Chemical class 0.000 claims description 14
- 150000001768 cations Chemical class 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 238000006317 isomerization reaction Methods 0.000 claims description 9
- 150000002736 metal compounds Chemical class 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 229910001507 metal halide Inorganic materials 0.000 claims description 4
- 150000005309 metal halides Chemical class 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 claims description 4
- 230000008707 rearrangement Effects 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 229940100198 alkylating agent Drugs 0.000 claims description 3
- 229910052747 lanthanoid Inorganic materials 0.000 claims description 3
- 150000002602 lanthanoids Chemical class 0.000 claims description 3
- 238000007336 electrophilic substitution reaction Methods 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 abstract description 4
- 229910052791 calcium Inorganic materials 0.000 abstract description 3
- 229910052733 gallium Inorganic materials 0.000 abstract description 3
- 229910052738 indium Inorganic materials 0.000 abstract description 3
- 229910052684 Cerium Inorganic materials 0.000 abstract description 2
- 229910052737 gold Inorganic materials 0.000 abstract description 2
- 229910052712 strontium Inorganic materials 0.000 abstract description 2
- 229910052716 thallium Inorganic materials 0.000 abstract description 2
- 229910052727 yttrium Inorganic materials 0.000 abstract description 2
- 229910052692 Dysprosium Inorganic materials 0.000 abstract 1
- 229910052691 Erbium Inorganic materials 0.000 abstract 1
- 229910052693 Europium Inorganic materials 0.000 abstract 1
- 229910052688 Gadolinium Inorganic materials 0.000 abstract 1
- 229910052689 Holmium Inorganic materials 0.000 abstract 1
- 229910052765 Lutetium Inorganic materials 0.000 abstract 1
- 229910052779 Neodymium Inorganic materials 0.000 abstract 1
- 229910052777 Praseodymium Inorganic materials 0.000 abstract 1
- 229910052772 Samarium Inorganic materials 0.000 abstract 1
- 229910052771 Terbium Inorganic materials 0.000 abstract 1
- 229910052775 Thulium Inorganic materials 0.000 abstract 1
- 229910052735 hafnium Inorganic materials 0.000 abstract 1
- 229910021481 rutherfordium Inorganic materials 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 112
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
- 239000000047 product Substances 0.000 description 46
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 41
- 239000000203 mixture Substances 0.000 description 38
- 238000010992 reflux Methods 0.000 description 33
- IQQRAVYLUAZUGX-UHFFFAOYSA-N 1-butyl-3-methylimidazolium Chemical compound CCCCN1C=C[N+](C)=C1 IQQRAVYLUAZUGX-UHFFFAOYSA-N 0.000 description 32
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 31
- 239000003208 petroleum Substances 0.000 description 28
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 26
- 238000004817 gas chromatography Methods 0.000 description 25
- 239000002904 solvent Substances 0.000 description 25
- 238000004458 analytical method Methods 0.000 description 21
- 238000009835 boiling Methods 0.000 description 21
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 18
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 18
- 239000001257 hydrogen Substances 0.000 description 17
- 229910052739 hydrogen Inorganic materials 0.000 description 17
- NJMWOUFKYKNWDW-UHFFFAOYSA-N 1-ethyl-3-methylimidazolium Chemical compound CCN1C=C[N+](C)=C1 NJMWOUFKYKNWDW-UHFFFAOYSA-N 0.000 description 16
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 16
- ZXMGHDIOOHOAAE-UHFFFAOYSA-N 1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F ZXMGHDIOOHOAAE-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical group CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 150000002431 hydrogen Chemical class 0.000 description 12
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 12
- 239000000376 reactant Substances 0.000 description 12
- CKGKXGQVRVAKEA-UHFFFAOYSA-N (2-methylphenyl)-phenylmethanone Chemical compound CC1=CC=CC=C1C(=O)C1=CC=CC=C1 CKGKXGQVRVAKEA-UHFFFAOYSA-N 0.000 description 11
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 11
- 239000011701 zinc Substances 0.000 description 11
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- AMNCGUPXVJYAEB-UHFFFAOYSA-N zinc 1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound [Zn++].FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F.FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F AMNCGUPXVJYAEB-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 9
- 229910052725 zinc Inorganic materials 0.000 description 9
- 150000001450 anions Chemical class 0.000 description 8
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 8
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 8
- RNQMMBCVKVCWTG-UHFFFAOYSA-N nickel(2+) 1,1,1-trifluoro-N-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound [Ni++].FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F.FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F RNQMMBCVKVCWTG-UHFFFAOYSA-N 0.000 description 8
- 238000000638 solvent extraction Methods 0.000 description 8
- 238000000023 Kugelrohr distillation Methods 0.000 description 7
- 238000005917 acylation reaction Methods 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 239000012965 benzophenone Substances 0.000 description 7
- 238000006471 dimerization reaction Methods 0.000 description 7
- 239000012259 ether extract Substances 0.000 description 7
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 6
- 238000005804 alkylation reaction Methods 0.000 description 6
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 238000005292 vacuum distillation Methods 0.000 description 6
- 239000005711 Benzoic acid Substances 0.000 description 5
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 5
- 150000001336 alkenes Chemical class 0.000 description 5
- 230000029936 alkylation Effects 0.000 description 5
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 235000010233 benzoic acid Nutrition 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 229940078552 o-xylene Drugs 0.000 description 5
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 238000006480 benzoylation reaction Methods 0.000 description 4
- ZNMCPMGVADPPIW-UHFFFAOYSA-N bis(trifluoromethylsulfonyl)azanide 1-butyl-3-methylimidazol-3-ium Chemical compound CCCCn1cc[n+](C)c1.CCCCn1cc[n+](C)c1.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F.FC(F)(F)S(=O)(=O)[N-]S(=O)(=O)C(F)(F)F ZNMCPMGVADPPIW-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 4
- 239000011133 lead Substances 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- GRUODACYFFPYCV-UHFFFAOYSA-N 2-(4-methylphenoxy)benzoic acid Chemical compound C1=CC(C)=CC=C1OC1=CC=CC=C1C(O)=O GRUODACYFFPYCV-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229910017052 cobalt Inorganic materials 0.000 description 3
- 239000010941 cobalt Substances 0.000 description 3
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229940069096 dodecene Drugs 0.000 description 3
- 239000002360 explosive Substances 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 229910052745 lead Inorganic materials 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
- CAXZJBXUESKEDG-UHFFFAOYSA-N octylbenzene Chemical compound [CH2-]CCCCCCCC1=CC=CC=C1 CAXZJBXUESKEDG-UHFFFAOYSA-N 0.000 description 3
- 238000001256 steam distillation Methods 0.000 description 3
- 150000003457 sulfones Chemical class 0.000 description 3
- 229910052723 transition metal Inorganic materials 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZSQCNVWYBBKUHS-UHFFFAOYSA-N (2,3-dimethylphenyl)-phenylmethanone Chemical compound CC1=CC=CC(C(=O)C=2C=CC=CC=2)=C1C ZSQCNVWYBBKUHS-UHFFFAOYSA-N 0.000 description 2
- OQERFUGURPLBQH-UHFFFAOYSA-N (2-hydroxy-5-methylphenyl)-phenylmethanone Chemical compound CC1=CC=C(O)C(C(=O)C=2C=CC=CC=2)=C1 OQERFUGURPLBQH-UHFFFAOYSA-N 0.000 description 2
- ZCVSDPUSEUOUHQ-UHFFFAOYSA-N 1-(benzenesulfonyl)-2,4-dimethylbenzene Chemical compound CC1=CC(C)=CC=C1S(=O)(=O)C1=CC=CC=C1 ZCVSDPUSEUOUHQ-UHFFFAOYSA-N 0.000 description 2
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 2
- GWVCFJWPVUOJNU-UHFFFAOYSA-N 4-chloro-1-(4-chloro-2-phenylphenyl)sulfonyl-2-phenylbenzene Chemical compound C=1C(Cl)=CC=C(S(=O)(=O)C=2C(=CC(Cl)=CC=2)C=2C=CC=CC=2)C=1C1=CC=CC=C1 GWVCFJWPVUOJNU-UHFFFAOYSA-N 0.000 description 2
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000005863 Friedel-Crafts acylation reaction Methods 0.000 description 2
- 238000005618 Fries rearrangement reaction Methods 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- VYRMUTVULWMCCO-UHFFFAOYSA-N N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.[Co] Chemical compound N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.[Co] VYRMUTVULWMCCO-UHFFFAOYSA-N 0.000 description 2
- WRQVTCDAGWYPMI-UHFFFAOYSA-N N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.[Fe+3] Chemical compound N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.[Fe+3] WRQVTCDAGWYPMI-UHFFFAOYSA-N 0.000 description 2
- UQUXIXQUAZLVIM-UHFFFAOYSA-N N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.[Sc] Chemical compound N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.[Sc] UQUXIXQUAZLVIM-UHFFFAOYSA-N 0.000 description 2
- AJMHJWGYPCSVNS-UHFFFAOYSA-N N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.[Zn] Chemical compound N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.N(S(=O)(=O)C(F)(F)F)S(=O)(=O)C(F)(F)F.[Zn] AJMHJWGYPCSVNS-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 2
- 229910052769 Ytterbium Inorganic materials 0.000 description 2
- PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 description 2
- XUNVQIVKWRBLPL-UHFFFAOYSA-N [Mg].FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F.FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F Chemical compound [Mg].FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F.FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F XUNVQIVKWRBLPL-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- YFZQCBAHLOLZQR-UHFFFAOYSA-N calcium;1,1,1-trifluoro-n-(trifluoromethylsulfonyl)methanesulfonamide Chemical compound [Ca].FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F.FC(F)(F)S(=O)(=O)NS(=O)(=O)C(F)(F)F YFZQCBAHLOLZQR-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- PDPJQWYGJJBYLF-UHFFFAOYSA-J hafnium tetrachloride Chemical compound Cl[Hf](Cl)(Cl)Cl PDPJQWYGJJBYLF-UHFFFAOYSA-J 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000011968 lewis acid catalyst Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical compound FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 238000006384 oligomerization reaction Methods 0.000 description 2
- 238000005191 phase separation Methods 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 238000000053 physical method Methods 0.000 description 2
- 238000004064 recycling Methods 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 238000005694 sulfonylation reaction Methods 0.000 description 2
- 230000036962 time dependent Effects 0.000 description 2
- 229910052718 tin Inorganic materials 0.000 description 2
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- GFPVQVVHZYIGOF-UHFFFAOYSA-N oct-1-en-2-ylbenzene Chemical compound CCCCCCC(=C)C1=CC=CC=C1 GFPVQVVHZYIGOF-UHFFFAOYSA-N 0.000 description 1
- LKSZOQMZRIERKX-UHFFFAOYSA-N oct-1-en-4-ylbenzene Chemical compound CCCCC(CC=C)C1=CC=CC=C1 LKSZOQMZRIERKX-UHFFFAOYSA-N 0.000 description 1
- IRUCBBFNLDIMIK-UHFFFAOYSA-N oct-4-ene Chemical compound CCCC=CCCC IRUCBBFNLDIMIK-UHFFFAOYSA-N 0.000 description 1
- 150000002891 organic anions Chemical class 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
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- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
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- 238000001556 precipitation Methods 0.000 description 1
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- 230000035484 reaction time Effects 0.000 description 1
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- 238000007086 side reaction Methods 0.000 description 1
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- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052714 tellurium Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
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- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
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- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0215—Sulfur-containing compounds
- B01J31/0225—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts
- B01J31/0227—Sulfur-containing compounds comprising sulfonic acid groups or the corresponding salts being perfluorinated, i.e. comprising at least one perfluorinated moiety as substructure in case of polyfunctional compounds
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- B01J31/0277—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature
- B01J31/0278—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre
- B01J31/0281—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member
- B01J31/0284—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing nitrogen as cationic centre the nitrogen being a ring member of an aromatic ring, e.g. pyridinium
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- B01J31/0287—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides comprising ionic liquids, as components in catalyst systems or catalysts per se, the ionic liquid compounds being used in the molten state at the respective reaction temperature containing atoms other than nitrogen as cationic centre
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/323—Hydrometalation, e.g. bor-, alumin-, silyl-, zirconation or analoguous reactions like carbometalation, hydrocarbation
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
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- Engineering & Computer Science (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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- Physical Vapour Deposition (AREA)
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GBGB0106000.3A GB0106000D0 (en) | 2001-03-12 | 2001-03-12 | Use of metal triflimide catalysts for the catalysis of chemical reactions |
PCT/GB2002/000988 WO2002072519A2 (fr) | 2001-03-12 | 2002-03-12 | Procede catalyse par des composes bis-triflimides |
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GB0123597D0 (en) * | 2001-10-02 | 2001-11-21 | Univ Belfast | Friedal-crafts reactions |
GB0123595D0 (en) | 2001-10-02 | 2001-11-21 | Univ Belfast | Zeolite reactions |
JP2004200015A (ja) * | 2002-12-19 | 2004-07-15 | Sanyo Electric Co Ltd | 非水電池用電解質及びその製造方法並びに非水電池用電解液 |
EP1658268B1 (fr) * | 2003-07-17 | 2014-02-12 | Novartis AG | Mélanges de liquides ioniques avec des acides de lewis |
ES2238013B1 (es) * | 2004-01-21 | 2006-11-01 | Institut Univ De Ciencia I Tecnologia | Procedimiento de acilacion de friedel-crafts en liquidos ionicos. |
JP4791092B2 (ja) * | 2005-06-30 | 2011-10-12 | ステラケミファ株式会社 | スルホニルイミド酸銀の製造方法 |
FR2889519B1 (fr) * | 2005-08-04 | 2008-07-11 | Rhodia Chimie Sa | Procede de c-alkylation de composes aromatiques hydroxyles avec un catalyseur de type tfsih |
EP2196486A1 (fr) * | 2008-12-12 | 2010-06-16 | Total Petrochemicals Research Feluy | Procédé de préparation de copolymères di et multi-bloc |
EP2401077A1 (fr) | 2009-02-26 | 2012-01-04 | Dow Global Technologies LLC | Procédés d'alcoxylation et catalyseurs correspondants |
JP5471045B2 (ja) * | 2009-06-03 | 2014-04-16 | セントラル硝子株式会社 | イミド酸塩の製造方法 |
JP5116048B2 (ja) * | 2010-03-10 | 2013-01-09 | 独立行政法人科学技術振興機構 | 触媒および反応方法 |
EP2581133A4 (fr) * | 2010-06-10 | 2014-04-30 | Ube Industries | Catalyseur d'alkylation et procédé de production d'un composé d'hydrocarbure aromatique alkylé à l'aide dudit catalyseur |
WO2014197834A1 (fr) | 2013-06-06 | 2014-12-11 | Halliburton Energy Services, Inc. | Traitement de puits pour perte de fluide |
CN103449986B (zh) * | 2013-09-27 | 2015-03-11 | 盐城美茵新材料有限公司 | 一种制备高纯度2,4`-二氟二苯甲酮的方法 |
WO2016004189A1 (fr) | 2014-07-03 | 2016-01-07 | Nulwala Hunaid B | Compositions sélectionnées pour procédés et dispositifs à base d'aluminium |
US10294325B2 (en) | 2016-01-04 | 2019-05-21 | National Technology & Engineering Solutions Of Sandia, Llc | Halo-containing anion exchange membranes and methods thereof |
US10053535B2 (en) | 2016-01-04 | 2018-08-21 | National Technology & Engineering Solutions Of Sandia, Llc | Poly(phenylene)-based anion exchange polymers and methods thereof |
WO2017120250A1 (fr) * | 2016-01-04 | 2017-07-13 | Sandia Corporation | Fonctionnalisation de polyphénylène diels-alder |
JP2017140792A (ja) * | 2016-02-12 | 2017-08-17 | 国立大学法人東北大学 | セキュリティーマーカー、情報記録媒体、情報記録媒体の判定装置及び複製装置 |
US10479866B1 (en) | 2018-02-28 | 2019-11-19 | National Technology & Engineering Solutions Of Sandia, Llc | Block copolymers including poly(phenylene) and methods thereof |
JP2019151602A (ja) * | 2018-03-05 | 2019-09-12 | 国立大学法人京都大学 | 金属イミド錯体及びこれを用いた基質変換方法 |
EP3698420B1 (fr) | 2018-04-17 | 2021-03-03 | Toyota Motor Europe | Les additifs et les méthodes pour ajouter des additifs dans une batterie non-aqueuse rechargeable de lithium et aérienne |
CN112004796B (zh) * | 2018-04-27 | 2023-06-06 | 株式会社力森诺科 | N,n-二取代酰胺的制造方法及用于制造n,n-二取代酰胺的催化剂 |
JP2020063349A (ja) * | 2018-10-16 | 2020-04-23 | 国立大学法人京都大学 | セルロース及び/又はヘミセルロースの製造方法 |
US20230027298A1 (en) * | 2019-12-12 | 2023-01-26 | The Regents Of The University Of California | Methods of Hydroarylation with Acid Catalysts |
CN113321669B (zh) * | 2020-02-28 | 2023-03-24 | 中国科学院上海有机化学研究所 | 一种磺酰亚胺类金属盐、其制备方法及应用 |
CN111303204B (zh) * | 2020-03-23 | 2022-09-23 | 沈阳师范大学 | 一种含有噻唑功能基团的二维金属有机配合物及其制备方法和应用 |
CN112778789B (zh) * | 2021-01-06 | 2021-11-12 | 贺潇寒 | 一种氯化蓝蒽酮、紫蒽酮或异紫蒽酮的方法 |
CN115028557B (zh) * | 2022-06-30 | 2023-08-01 | 中船(邯郸)派瑞特种气体股份有限公司 | 一种节约成本的n-苯基双三氟甲磺酰亚胺的制备方法 |
CN117185965B (zh) * | 2023-09-18 | 2024-10-11 | 安徽金桐精细化学有限公司 | 一种磺酸基丙烯酸盐复配表面活性剂的制备方法 |
CN117886683A (zh) * | 2024-03-15 | 2024-04-16 | 山东德澳精细化学品有限公司 | 一种间氯苯丙酮的制备方法 |
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US3098099A (en) * | 1960-04-19 | 1963-07-16 | Union Carbide Corp | Ester-ketone conversion |
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US5874616A (en) * | 1995-03-06 | 1999-02-23 | Minnesota Mining And Manufacturing Company | Preparation of bis (fluoroalkylenesulfonyl) imides and (fluoroalkysulfony) (fluorosulfonyl) imides |
JPH0957110A (ja) * | 1995-08-28 | 1997-03-04 | Central Glass Co Ltd | ルイス酸触媒 |
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JP3788525B2 (ja) * | 1996-01-09 | 2006-06-21 | セントラル硝子株式会社 | スカンジウム−パーフルオロアルカンスルホニルイミド錯体およびその製造方法 |
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JPH09241315A (ja) * | 1996-03-08 | 1997-09-16 | Central Glass Co Ltd | ポリオレフィン類の製造方法 |
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2002
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- 2002-03-12 EP EP07010851A patent/EP1857432A3/fr not_active Withdrawn
- 2002-03-12 DE DE60221991T patent/DE60221991T2/de not_active Expired - Lifetime
- 2002-03-12 EP EP02704905A patent/EP1370508A2/fr not_active Withdrawn
- 2002-03-12 CA CA002440937A patent/CA2440937A1/fr not_active Abandoned
- 2002-03-12 AU AU2002241085A patent/AU2002241085B2/en not_active Ceased
- 2002-03-12 KR KR10-2003-7011956A patent/KR20030093236A/ko not_active Application Discontinuation
- 2002-03-12 CA CA002440942A patent/CA2440942A1/fr not_active Abandoned
- 2002-03-12 WO PCT/GB2002/000988 patent/WO2002072519A2/fr active Application Filing
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- 2002-03-12 PT PT02706922T patent/PT1414568E/pt unknown
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Also Published As
Publication number | Publication date |
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CN1328254C (zh) | 2007-07-25 |
US20040138433A1 (en) | 2004-07-15 |
BR0208094A (pt) | 2004-03-02 |
EP1857432A3 (fr) | 2008-05-14 |
US7781625B2 (en) | 2010-08-24 |
DE60221991T2 (de) | 2008-05-15 |
AU2002238707A1 (en) | 2002-09-24 |
EP1414568B1 (fr) | 2007-08-22 |
US20040171895A1 (en) | 2004-09-02 |
WO2002072260A3 (fr) | 2004-02-26 |
US6998497B2 (en) | 2006-02-14 |
ATE370786T1 (de) | 2007-09-15 |
PT1414568E (pt) | 2007-12-04 |
JP2004531492A (ja) | 2004-10-14 |
CA2440937A1 (fr) | 2002-09-19 |
EP1414568A2 (fr) | 2004-05-06 |
CN1507371A (zh) | 2004-06-23 |
JP2004528306A (ja) | 2004-09-16 |
KR20030093236A (ko) | 2003-12-06 |
EP1857432A2 (fr) | 2007-11-21 |
ES2292722T3 (es) | 2008-03-16 |
AU2002241085B2 (en) | 2007-03-29 |
CA2440942A1 (fr) | 2002-09-19 |
WO2002072519A2 (fr) | 2002-09-19 |
WO2002072260A2 (fr) | 2002-09-19 |
WO2002072519A3 (fr) | 2002-11-21 |
EP1370508A2 (fr) | 2003-12-17 |
DE60221991D1 (de) | 2007-10-04 |
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